Aliphatic Ketones from Ruta chalepensis (Rutaceae) Induce Paralysis on Root Knot Nematodes

Department of Pharmaceutical Chemistry and Technology, University of Cagliari, Cagliari, Italy.
Journal of Agricultural and Food Chemistry (Impact Factor: 3.11). 06/2011; 59(13):7098-103. DOI: 10.1021/jf2013474
Source: PubMed

ABSTRACT This paper reports on the use of Ruta chalepensis L. extracts as a potential nematicide against root knot nematodes Meloidogyne incognita and Meloidogyne javanica . The essential oil (REO) and methanol extract (RME) of R. chalepensis were tested against second-stage juveniles, with REO inducing paralysis in both species (EC(50/1d) = 77.5 and 107.3 mg/L) and RME being selective for M. incognita (EC(50/1d) = 1001 mg/L). Chemical characterization of extracts was done by means of GC-MS and LC-MS, revealing mainly aliphatic ketones and coumarins, respectively. The first-ranking volatile nematicidal component in terms of individual activity against both species was 2-undecanone (EC(50) = 20.6 and 22.5 mg/L for M. incognita and M. javanica, respectively). This fact together with its high concentration in the most active extract found in this study, namely, REO (2926 mg/kg), categorizes 2-undecanone among the nematicidal principles of R. chalepensis. On the contrary, coumarins rutin and 8-methoxypsoralen were not found to be nematicidal at concentrations of ≤500 mg/L. Interestingly, M. incognita was found more sensitive than M. javanica.

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    • "R. graveolens EOs herewith studied showed very good B. xylophilus anti-nematodal activity. Ruta chalepensis EOs, also 2-undeca- none rich, showed also high activity against the root knot nematodes Meloidogyne incognita and M. javanica (Ntalli et al., 2011a). Other thymol and carvacrol-rich essential oils have also been reported to have high B. xylophilus anti-nematodal activity. "
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    ABSTRACT: The Portuguese pine forest has become dangerously threatened by pine wilt disease (PWD), caused by the pinewood nematode (PWN), Bursaphelenchus xylophilus. Synthetic chemicals are the most common pesticides used against phytoparasitic nematodes but its use has negative ecological impacts. Phytochemicals may prove to be environmentally friendly alternatives. Essential oils (EOs) and decoction waters, isolated from 84 plant samples, were tested against B. xylophilus, in direct contact assays. Some successful EOs were fractionated and the fractions containing hydrocarbons or oxygen-containing molecules tested separately. Twenty EOs showed corrected mortalities ⩾96% at 2 μL/mL. These were further tested at lower concentrations. Ruta graveolens, Satureja montana and Thymbra capitata EOs showed lethal concentrations (LC100)<0.4μL/mL. Oxygen-containing molecules fractions showing corrected mortality ⩾96% did not always show LC100 values similar to the corresponding EOs, suggesting additive and/or synergistic relationships among fractions. Nine decoction waters (remaining hydrodistillation waters) revealed 100% mortality at a minimum concentration of 12.5μL/mL. R. graveolens, S. montana and T. capitata EOs are potential environmentally friendly alternatives for B. xylophilus control given their high nematotoxic properties. Nematotoxic activity of an EO should be taken in its entirety, as its different components may contribute, in distinct ways, to the overall EO activity.
    Phytochemistry 07/2013; 94. DOI:10.1016/j.phytochem.2013.06.005 · 3.35 Impact Factor
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    • "The concentrates consist of a mixture of many volatile compounds, such as alcohols, aldehydes, ketones, esters, aromatic phenols, and lactones, as well as monoterpenes and sesquiterpenes . While the essential oils and their components have demonstrated a broad insecticidal or nematicidal activity [11] [12] [13], many previous studies have also shown that some essential oils or their constituents have showed a strong nematicidal activity, specifically against the pinewood nematode [14] [15] [16] [17] [18] [19] [20] [21] [22]. Although, the primary mode of action of these essential oils is unclear, an insight into its mechanism is necessary to enable efficient screening for effective nematicidal agents. "
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    Pesticide Biochemistry and Physiology 01/2013; 105(1):50-6. DOI:10.1016/j.pestbp.2012.11.007 · 2.01 Impact Factor
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    • "It has been proposed that an aldehyde group conjugated to a carbon to carbon double bond is a highly electronegative arrangement, which may explain their activity (Moleyar and Narasimham, 1986), suggesting an increase in electronegativity that increases the antibacterial activity (Kurita et al., 1979, 1981). The ketones such as 2-undecanone and undecanone were reported to have antimicrobial and nematicidal activity (Benhadj et al., 2007; Nikoletta et al., 2011). Aliphatic alcohols were reported to possess strong to moderate activities against several bacteria . "
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